Christine also has a game called Digital: A Love Story but I never really checked it out.

I have! Digital: A Love Story is my favourite Visual Novel. And yeah I haven't played all that many, but still, it's amazing. I really recommend it. It's so immersive and atmospheric and you get to be a HACKER and post on BULLETIN BOARDS and it's all RETRO INTERNET sdfghjkkm love it. Plus the story is great. You can download it for free right here.

In fact, if you'll permit a slight plug (but not really because the blog is totally dead) I did a review of it on a blog I used to keep. I also commissioned a guy called Mark, who does reviews of books and TV series and very occasionally games (he's the Mark behind Mark Reads Twilight if anyone here has heard of it) to play it and his impressions are pretty interesting. Slight plot spoilers though._________________If that's the worst you got, better put your fingers back to the keys.

I shamefully forgot about Magical Diary which looks anime campy as hell but is really deep and features an asexual romance partner. It also tackles issues like manipulation, a school's willingness to overlook criminal activity and family issues. It's pretty damn deep for what looks like a magical girl sim.

People who are interested in games that explore gender should check out Dierdra Kiai's stuff. Their game Dominique Pamplemousse was nominated for a bunch of IGF awards.

Also, while it's not quite in the same vein as the other games that have been mentioned, right now I'm playing The Cat Lady and loving into tiny pieces. The protagonist is a clinically depressed middle-aged woman, which I don't think I've seen anywhere else, and it passes the Bechdel test in the very first conversation.